9,9′-Dibromo-9,9′-bifluorene

Mizuhata, Y.; Tokitoh, N.

doi:10.1107/S160053680800295X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o544

doi:10.1107/S160053680800295X

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9,9′-Dibromo-9,9′-bifluorene

Yoshiyuki Mizuhata ^a and Norihiro Tokitoh ^a ^*

^aInstitute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan
^*Correspondence e-mail: tokitoh@boc.kuicr.kyoto-u.ac.jp

(Received 22 January 2008; accepted 26 January 2008; online 6 February 2008)

9,9′-Dibromo-9,9′-bifluorene, C₂₆H₁₆Br₂, has a gauche conformation about the connecting C—C bond [the Br—C—C—Br torsion angle is 59.39 (16)°]. The crystal structure is sustained mainly by an intermolecular C—Br⋯π interaction [3.299 (2) and 3.369 (2) Å] towards the bifluorene aromatic-ring-connecting C—C bond and a weak C—H⋯π interaction (2.86 and 2.99 Å) between the two aromatic rings.

Related literature

For related literature, see: Dougherty et al. (1978 ); Graebe & Manz (1896 ); Olah et al. (1981 ); Solans et al. (1980 ); Sridevi et al. (2006 ).

Experimental

Crystal data

C₂₆H₁₆Br₂
M_r = 488.21
Monoclinic, P 2₁ /n
a = 12.7083 (3) Å
b = 12.0480 (2) Å
c = 12.7786 (2) Å
β = 102.5340 (8)°
V = 1909.90 (6) Å³
Z = 4
Mo Kα radiation
μ = 4.25 mm⁻¹
T = 103 (2) K
0.30 × 0.10 × 0.10 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (REQUAB; Jacobson, 1998 ) T_min = 0.351, T_max = 0.655
12332 measured reflections
3339 independent reflections
3242 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.070
S = 1.12
3339 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.97 e Å⁻³

Table 1
Selected interatomic distances (Å)

Br2⋯C11ⁱ	3.299 (2)
Br2⋯C12ⁱ	3.369 (2)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H15⋯C2ⁱⁱ	0.95	2.99	3.760 (3)	140
C20—H15⋯C3ⁱⁱ	0.95	2.86	3.493 (3)	125
Symmetry code: (ii) -x+2, -y, -z+1.

Data collection: CrystalClear (Rigaku, 2004 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and Mercury (Version 1.4.2; Macrae et al., 2006 ); software used to prepare material for publication: yadokari-XG (Wakita, 2005 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800295X/sg2222sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680800295X/sg2222Isup2.hkl

checkCIF report

Comment top

Although a number of synthetic works and structural analyses on 9,9'-bifluorene derivertives have been reported, only one report is known for the crystalline structure of 9-halo-9,9'-bifluorene derivertive, that is, 1,1',2,2',3,3',4,4',5,5',6,6',7,7',8,8',9-heptadecachloro- 9,9'-bifluorene (Solans et al., 1980). We have succeeded in the first structural analysis of 9,9'-dihalo-9,9'-bifluorene derivertive, 9,9'-dibromo-9,9'-bifluorene.

The first report on the synthesis of 9,9'-dibromo-9,9'-bifluorene appaered in the 19t h century (Graebe et al., 1896). Its gauche groud-state conformation was revealed by its NMR spectra and the theoretical calculations (Olah et al., 1981).

The molecular structure of the title compound is shown in Fig. 1. The dihedral angle of Br1—C9—C22—Br2 is 59.39 (16)°, indicating its gauche conformation. Although the bond length of C9—C22 [1.561 (3) Å] is longer than that of non-substituted 9,9'-bifluorene [1.542 (3) Å, Dougherty et al., 1978; 1.539 (3) Å, Sridevi et al., 2006], it is one of the shortest C—C bonds between 9 and 9' positions among the 9(,9')-substituted 9,9'-bifluorenes (1.559–1.724 Å). The shortest intermolecular contacts were found to be C22—Br2···C11ⁱ [3.299 (2) Å], C22—Br2···C12ⁱ [3.369 (2) Å], and C20—H15···C3ⁱⁱ (2.86 Å) (Fig. 2) [symmetry codes: (i) 3/2 - x, -1/2 + y, 1/2 - z, (ii) 2 - x, -y, 1 - z].

Related literature top

For related literature, see: Dougherty et al. (1978); Graebe & Manz (1896); Olah et al. (1981); Solans et al. (1980); Sridevi et al. (2006).

Computing details top

Data collection: CrystalClear (Rigaku, 2004); cell refinement: CrystalClear (Rigaku, 2004); data reduction: CrystalClear (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Version 1.4.2; Macrae et al., 2006); software used to prepare material for publication: yadokari-XG (Wakita, 2005).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The molecular packing of the title compound. Dashed lines indicate the intermolecular contacts [symmetry codes: (i) 3/2 - x, -1/2 + y, 1/2 - z, (ii) 2 - x, -y, 1 - z].

9,9'-Dibromo-9,9'-bifluorene top

Crystal data top

C₂₆H₁₆Br₂	Z = 4
M_r = 488.21	F(000) = 968
Monoclinic, P2₁/n	D_x = 1.698 Mg m⁻³
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71069 Å
a = 12.7083 (3) Å	θ = 3.1–25.0°
b = 12.0480 (2) Å	µ = 4.25 mm⁻¹
c = 12.7786 (2) Å	T = 103 K
β = 102.5340 (8)°	Prism, colorless
V = 1909.90 (6) Å³	0.30 × 0.10 × 0.10 mm

Data collection top

Rigaku Mercury CCD diffractometer	3339 independent reflections
Radiation source: fine-focus sealed tube	3242 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 25.0°, θ_min = 3.1°
Absorption correction: multi-scan (REQUAB; Jacobson, 1998)	h = −15→11
T_min = 0.351, T_max = 0.655	k = −14→14
12332 measured reflections	l = −11→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.070	w = 1/[σ²(F_o²) + (0.0444P)² + 0.8804P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.001
3339 reflections	Δρ_max = 0.48 e Å⁻³
254 parameters	Δρ_min = −0.97 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0188 (9)

Crystal data top

C₂₆H₁₆Br₂	V = 1909.90 (6) Å³
M_r = 488.21	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.7083 (3) Å	µ = 4.25 mm⁻¹
b = 12.0480 (2) Å	T = 103 K
c = 12.7786 (2) Å	0.30 × 0.10 × 0.10 mm
β = 102.5340 (8)°

Data collection top

Rigaku Mercury CCD diffractometer	3339 independent reflections
Absorption correction: multi-scan (REQUAB; Jacobson, 1998)	3242 reflections with I > 2σ(I)
T_min = 0.351, T_max = 0.655	R_int = 0.039
12332 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 1.12	Δρ_max = 0.48 e Å⁻³
3339 reflections	Δρ_min = −0.97 e Å⁻³
254 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.84656 (18)	0.16573 (18)	0.23137 (17)	0.0212 (4)
H1	0.7992	0.1271	0.1755	0.025*
C2	0.95781 (19)	0.15777 (19)	0.24391 (19)	0.0253 (5)
H2	0.9867	0.1129	0.1959	0.030*
C3	1.02751 (18)	0.21444 (19)	0.3257 (2)	0.0261 (5)
H3	1.1032	0.2067	0.3332	0.031*
C4	0.98803 (18)	0.28206 (18)	0.39616 (18)	0.0227 (5)
H4	1.0356	0.3213	0.4514	0.027*
C5	0.84633 (19)	0.43653 (19)	0.52326 (17)	0.0241 (5)
H5	0.9206	0.4459	0.5551	0.029*
C6	0.7676 (2)	0.4993 (2)	0.55742 (18)	0.0270 (5)
H6	0.7885	0.5524	0.6130	0.032*
C7	0.6587 (2)	0.48479 (18)	0.51094 (18)	0.0254 (5)
H7	0.6063	0.5289	0.5345	0.031*
C8	0.62552 (18)	0.40646 (17)	0.43032 (17)	0.0214 (4)
H8	0.5512	0.3961	0.3993	0.026*
C9	0.69082 (16)	0.25349 (16)	0.31151 (16)	0.0165 (4)
C10	0.80673 (17)	0.23199 (16)	0.30326 (16)	0.0174 (4)
C11	0.87685 (17)	0.29089 (17)	0.38378 (17)	0.0195 (4)
C12	0.81287 (17)	0.36011 (17)	0.44157 (16)	0.0189 (4)
C13	0.70351 (18)	0.34400 (17)	0.39632 (16)	0.0180 (4)
C14	0.42727 (17)	0.20938 (17)	0.30227 (18)	0.0196 (4)
H9	0.4246	0.2216	0.2283	0.024*
C15	0.33643 (18)	0.22638 (17)	0.34502 (19)	0.0223 (5)
H10	0.2715	0.2515	0.2995	0.027*
C16	0.33917 (18)	0.20728 (18)	0.45294 (19)	0.0237 (5)
H11	0.2765	0.2204	0.4804	0.028*
C17	0.43250 (19)	0.16928 (17)	0.52080 (18)	0.0212 (4)
H12	0.4340	0.1546	0.5942	0.025*
C18	0.67213 (19)	0.07827 (17)	0.63627 (17)	0.0224 (5)
H13	0.6286	0.0808	0.6880	0.027*
C19	0.7776 (2)	0.04043 (17)	0.66387 (19)	0.0241 (5)
H14	0.8070	0.0184	0.7356	0.029*
C20	0.84104 (19)	0.03434 (17)	0.58756 (18)	0.0223 (5)
H15	0.9131	0.0081	0.6080	0.027*
C21	0.79998 (17)	0.06636 (17)	0.48168 (17)	0.0195 (4)
H16	0.8424	0.0603	0.4292	0.023*
C22	0.63207 (16)	0.15126 (16)	0.34754 (15)	0.0161 (4)
C23	0.52149 (17)	0.17426 (16)	0.37060 (16)	0.0167 (4)
C24	0.52399 (17)	0.15302 (16)	0.47932 (16)	0.0178 (4)
C25	0.63132 (17)	0.11255 (16)	0.53100 (16)	0.0182 (4)
C26	0.69575 (17)	0.10723 (16)	0.45519 (16)	0.0169 (4)
Br1	0.611538 (16)	0.312530 (17)	0.171820 (15)	0.02031 (11)
Br2	0.616445 (16)	0.029301 (16)	0.241602 (16)	0.02030 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0244 (11)	0.0232 (10)	0.0175 (10)	0.0005 (8)	0.0074 (9)	0.0037 (9)
C2	0.0270 (12)	0.0252 (11)	0.0271 (12)	0.0070 (9)	0.0131 (10)	0.0082 (10)
C3	0.0188 (11)	0.0271 (11)	0.0334 (13)	0.0031 (9)	0.0082 (10)	0.0119 (10)
C4	0.0196 (11)	0.0224 (10)	0.0242 (11)	−0.0016 (8)	0.0003 (9)	0.0085 (9)
C5	0.0277 (12)	0.0251 (11)	0.0170 (11)	−0.0068 (9)	−0.0005 (9)	0.0024 (9)
C6	0.0407 (14)	0.0228 (11)	0.0182 (11)	−0.0077 (10)	0.0080 (10)	−0.0052 (9)
C7	0.0356 (13)	0.0215 (11)	0.0217 (11)	−0.0012 (9)	0.0117 (10)	−0.0037 (9)
C8	0.0253 (11)	0.0184 (10)	0.0214 (11)	−0.0017 (8)	0.0068 (9)	−0.0005 (8)
C9	0.0195 (10)	0.0178 (9)	0.0114 (9)	0.0013 (8)	0.0021 (8)	0.0004 (8)
C10	0.0195 (10)	0.0175 (10)	0.0153 (10)	0.0016 (8)	0.0044 (8)	0.0056 (8)
C11	0.0222 (11)	0.0183 (10)	0.0177 (10)	−0.0001 (8)	0.0040 (9)	0.0081 (8)
C12	0.0245 (11)	0.0178 (10)	0.0143 (10)	−0.0026 (8)	0.0037 (8)	0.0043 (8)
C13	0.0249 (11)	0.0157 (9)	0.0135 (10)	−0.0019 (8)	0.0046 (8)	0.0023 (8)
C14	0.0215 (11)	0.0179 (10)	0.0198 (11)	−0.0017 (8)	0.0051 (9)	0.0000 (8)
C15	0.0192 (11)	0.0194 (10)	0.0275 (12)	0.0002 (8)	0.0034 (9)	−0.0002 (9)
C16	0.0236 (11)	0.0199 (10)	0.0303 (12)	−0.0014 (8)	0.0116 (10)	−0.0023 (9)
C17	0.0288 (12)	0.0175 (10)	0.0190 (11)	−0.0024 (8)	0.0088 (9)	−0.0018 (8)
C18	0.0330 (12)	0.0196 (10)	0.0146 (10)	−0.0012 (9)	0.0049 (9)	−0.0005 (8)
C19	0.0323 (13)	0.0210 (10)	0.0162 (11)	−0.0012 (9)	−0.0008 (9)	0.0021 (8)
C20	0.0240 (12)	0.0174 (10)	0.0221 (11)	0.0009 (8)	−0.0021 (9)	0.0031 (8)
C21	0.0225 (11)	0.0153 (10)	0.0203 (11)	−0.0006 (8)	0.0035 (8)	0.0007 (8)
C22	0.0205 (11)	0.0154 (9)	0.0118 (9)	−0.0003 (8)	0.0023 (8)	−0.0037 (8)
C23	0.0196 (11)	0.0143 (9)	0.0164 (10)	−0.0027 (7)	0.0044 (8)	−0.0031 (8)
C24	0.0231 (11)	0.0136 (9)	0.0167 (10)	−0.0027 (8)	0.0044 (8)	−0.0032 (8)
C25	0.0249 (11)	0.0125 (9)	0.0167 (10)	−0.0021 (8)	0.0035 (9)	−0.0021 (8)
C26	0.0229 (10)	0.0132 (9)	0.0141 (10)	−0.0021 (8)	0.0026 (8)	−0.0007 (7)
Br1	0.02204 (15)	0.02365 (15)	0.01439 (15)	0.00219 (7)	0.00212 (9)	0.00367 (7)
Br2	0.02386 (16)	0.01924 (15)	0.01694 (14)	0.00053 (7)	0.00257 (9)	−0.00527 (7)

Geometric parameters (Å, º) top

C1—C2	1.391 (3)	C14—C23	1.386 (3)
C1—C10	1.393 (3)	C14—C15	1.395 (3)
C1—H1	0.9500	C14—H9	0.9500
C2—C3	1.393 (4)	C15—C16	1.391 (3)
C2—H2	0.9500	C15—H10	0.9500
C3—C4	1.387 (3)	C16—C17	1.386 (3)
C3—H3	0.9500	C16—H11	0.9500
C4—C11	1.391 (3)	C17—C24	1.392 (3)
C4—H4	0.9500	C17—H12	0.9500
C5—C12	1.388 (3)	C18—C19	1.387 (3)
C5—C6	1.398 (4)	C18—C25	1.395 (3)
C5—H5	0.9500	C18—H13	0.9500
C6—C7	1.394 (4)	C19—C20	1.395 (3)
C6—H6	0.9500	C19—H14	0.9500
C7—C8	1.393 (3)	C20—C21	1.395 (3)
C7—H7	0.9500	C20—H15	0.9500
C8—C13	1.387 (3)	C21—C26	1.385 (3)
C8—H8	0.9500	C21—H16	0.9500
C9—C13	1.521 (3)	C22—C23	1.523 (3)
C9—C10	1.522 (3)	C22—C26	1.531 (3)
C9—C22	1.561 (3)	C22—Br2	1.9785 (19)
C9—Br1	1.982 (2)	C23—C24	1.406 (3)
C10—C11	1.399 (3)	C24—C25	1.464 (3)
C11—C12	1.470 (3)	C25—C26	1.399 (3)
C12—C13	1.398 (3)

Br2···C11ⁱ	3.299 (2)	Br2···C12ⁱ	3.369 (2)

C2—C1—C10	118.0 (2)	C23—C14—C15	118.2 (2)
C2—C1—H1	121.0	C23—C14—H9	120.9
C10—C1—H1	121.0	C15—C14—H9	120.9
C1—C2—C3	121.2 (2)	C16—C15—C14	121.3 (2)
C1—C2—H2	119.4	C16—C15—H10	119.4
C3—C2—H2	119.4	C14—C15—H10	119.4
C4—C3—C2	120.9 (2)	C17—C16—C15	120.6 (2)
C4—C3—H3	119.5	C17—C16—H11	119.7
C2—C3—H3	119.5	C15—C16—H11	119.7
C3—C4—C11	118.2 (2)	C16—C17—C24	118.7 (2)
C3—C4—H4	120.9	C16—C17—H12	120.7
C11—C4—H4	120.9	C24—C17—H12	120.7
C12—C5—C6	118.1 (2)	C19—C18—C25	118.6 (2)
C12—C5—H5	121.0	C19—C18—H13	120.7
C6—C5—H5	121.0	C25—C18—H13	120.7
C7—C6—C5	120.8 (2)	C18—C19—C20	120.8 (2)
C7—C6—H6	119.6	C18—C19—H14	119.6
C5—C6—H6	119.6	C20—C19—H14	119.6
C8—C7—C6	120.9 (2)	C21—C20—C19	120.8 (2)
C8—C7—H7	119.6	C21—C20—H15	119.6
C6—C7—H7	119.6	C19—C20—H15	119.6
C13—C8—C7	118.5 (2)	C26—C21—C20	118.2 (2)
C13—C8—H8	120.8	C26—C21—H16	120.9
C7—C8—H8	120.8	C20—C21—H16	120.9
C13—C9—C10	102.52 (16)	C23—C22—C26	102.66 (16)
C13—C9—C22	109.82 (16)	C23—C22—C9	115.74 (16)
C10—C9—C22	114.74 (16)	C26—C22—C9	110.18 (16)
C13—C9—Br1	109.82 (13)	C23—C22—Br2	107.92 (13)
C10—C9—Br1	108.01 (13)	C26—C22—Br2	108.20 (13)
C22—C9—Br1	111.52 (13)	C9—C22—Br2	111.57 (13)
C1—C10—C11	120.7 (2)	C14—C23—C24	120.61 (19)
C1—C10—C9	129.73 (19)	C14—C23—C22	129.87 (19)
C11—C10—C9	109.53 (18)	C24—C23—C22	109.52 (18)
C4—C11—C10	120.9 (2)	C17—C24—C23	120.6 (2)
C4—C11—C12	130.1 (2)	C17—C24—C25	130.42 (19)
C10—C11—C12	108.88 (18)	C23—C24—C25	108.98 (18)
C5—C12—C13	121.2 (2)	C18—C25—C26	120.2 (2)
C5—C12—C11	129.9 (2)	C18—C25—C24	130.43 (19)
C13—C12—C11	108.78 (18)	C26—C25—C24	109.33 (18)
C8—C13—C12	120.6 (2)	C21—C26—C25	121.31 (19)
C8—C13—C9	129.8 (2)	C21—C26—C22	129.33 (18)
C12—C13—C9	109.65 (18)	C25—C26—C22	109.36 (17)

C10—C1—C2—C3	−0.1 (3)	C19—C20—C21—C26	1.8 (3)
C1—C2—C3—C4	−1.0 (3)	C13—C9—C22—C23	57.5 (2)
C2—C3—C4—C11	0.7 (3)	C10—C9—C22—C23	172.27 (17)
C12—C5—C6—C7	0.3 (3)	Br1—C9—C22—C23	−64.52 (19)
C5—C6—C7—C8	0.9 (3)	C13—C9—C22—C26	−58.4 (2)
C6—C7—C8—C13	−0.8 (3)	C10—C9—C22—C26	56.4 (2)
C2—C1—C10—C11	1.6 (3)	Br1—C9—C22—C26	179.60 (13)
C2—C1—C10—C9	−177.91 (19)	C13—C9—C22—Br2	−178.64 (13)
C13—C9—C10—C1	−172.8 (2)	C10—C9—C22—Br2	−63.81 (19)
C22—C9—C10—C1	68.2 (3)	Br1—C9—C22—Br2	59.39 (16)
Br1—C9—C10—C1	−56.9 (2)	C15—C14—C23—C24	2.0 (3)
C13—C9—C10—C11	7.6 (2)	C15—C14—C23—C22	−178.76 (19)
C22—C9—C10—C11	−111.41 (19)	C26—C22—C23—C14	−175.8 (2)
Br1—C9—C10—C11	123.53 (15)	C9—C22—C23—C14	64.1 (3)
C3—C4—C11—C10	0.8 (3)	Br2—C22—C23—C14	−61.7 (2)
C3—C4—C11—C12	−176.1 (2)	C26—C22—C23—C24	3.5 (2)
C1—C10—C11—C4	−2.0 (3)	C9—C22—C23—C24	−116.61 (19)
C9—C10—C11—C4	177.61 (18)	Br2—C22—C23—C24	117.60 (15)
C1—C10—C11—C12	175.47 (18)	C16—C17—C24—C23	−0.3 (3)
C9—C10—C11—C12	−4.9 (2)	C16—C17—C24—C25	−178.9 (2)
C6—C5—C12—C13	−1.6 (3)	C14—C23—C24—C17	−1.4 (3)
C6—C5—C12—C11	174.0 (2)	C22—C23—C24—C17	179.19 (18)
C4—C11—C12—C5	1.0 (4)	C14—C23—C24—C25	177.42 (17)
C10—C11—C12—C5	−176.2 (2)	C22—C23—C24—C25	−1.9 (2)
C4—C11—C12—C13	177.0 (2)	C19—C18—C25—C26	0.8 (3)
C10—C11—C12—C13	−0.2 (2)	C19—C18—C25—C24	178.3 (2)
C7—C8—C13—C12	−0.5 (3)	C17—C24—C25—C18	0.4 (4)
C7—C8—C13—C9	179.6 (2)	C23—C24—C25—C18	−178.3 (2)
C5—C12—C13—C8	1.7 (3)	C17—C24—C25—C26	178.1 (2)
C11—C12—C13—C8	−174.74 (18)	C23—C24—C25—C26	−0.6 (2)
C5—C12—C13—C9	−178.35 (18)	C20—C21—C26—C25	−2.5 (3)
C11—C12—C13—C9	5.2 (2)	C20—C21—C26—C22	177.94 (19)
C10—C9—C13—C8	172.2 (2)	C18—C25—C26—C21	1.2 (3)
C22—C9—C13—C8	−65.4 (3)	C24—C25—C26—C21	−176.82 (18)
Br1—C9—C13—C8	57.6 (3)	C18—C25—C26—C22	−179.13 (17)
C10—C9—C13—C12	−7.7 (2)	C24—C25—C26—C22	2.9 (2)
C22—C9—C13—C12	114.67 (19)	C23—C22—C26—C21	175.8 (2)
Br1—C9—C13—C12	−122.35 (15)	C9—C22—C26—C21	−60.3 (3)
C23—C14—C15—C16	−0.9 (3)	Br2—C22—C26—C21	61.9 (2)
C14—C15—C16—C17	−0.8 (3)	C23—C22—C26—C25	−3.8 (2)
C15—C16—C17—C24	1.4 (3)	C9—C22—C26—C25	120.03 (18)
C25—C18—C19—C20	−1.4 (3)	Br2—C22—C26—C25	−117.75 (15)
C18—C19—C20—C21	0.1 (3)

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H15···C2ⁱⁱ	0.95	2.99	3.760 (3)	140
C20—H15···C3ⁱⁱ	0.95	2.86	3.493 (3)	125

Symmetry code: (ii) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₆Br₂
M_r	488.21
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	103
a, b, c (Å)	12.7083 (3), 12.0480 (2), 12.7786 (2)
β (°)	102.5340 (8)
V (Å³)	1909.90 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.25
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (REQUAB; Jacobson, 1998)
T_min, T_max	0.351, 0.655
No. of measured, independent and observed [I > 2σ(I)] reflections	12332, 3339, 3242
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.070, 1.12
No. of reflections	3339
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.97

Computer programs: CrystalClear (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and Mercury (Version 1.4.2; Macrae et al., 2006), yadokari-XG (Wakita, 2005).

Selected interatomic distances (Å) top

Br2···C11ⁱ

3.299 (2)

Br2···C12ⁱ

3.369 (2)

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H15···C2ⁱⁱ	0.95	2.99	3.760 (3)	139.56
C20—H15···C3ⁱⁱ	0.95	2.86	3.493 (3)	124.73

Symmetry code: (ii) −x+2, −y, −z+1.

Acknowledgements

This work was partially supported by Grants-in-Aid for Creative Scientific Research (No. 17GS0207), the 21st Century COE Program B14 (Kyoto University Alliance for Chemistry), and the Global COE Program B09 (International Center for Integrated Research and Advanced Education in Materials Science) from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

References

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